5-(O-p-toluenesulfonyl)-4-C-(p-toluenesulfonyloxymethyl)-1,2-O-(isopropylidene)-β-L-threo-xylofuranose

Base Information

• Chemical Name: 5-(O-p-toluenesulfonyl)-4-C-(p-toluenesulfonyloxymethyl)-1,2-O-(isopropylidene)-β-L-threo-xylofuranose
• CAS No.: 551934-26-0
• Molecular Formula: C₂₃H₂₈O₁₀S₂
• Molecular Weight: 528.601

Synonyms:5-(O-p-toluenesulfonyl)-4-C-(p-toluenesulfonyloxymethyl)-1,2-O-(isopropylidene)-β-L-threo-xylofuranose

Chemical Property of 5-(O-p-toluenesulfonyl)-4-C-(p-toluenesulfonyloxymethyl)-1,2-O-(isopropylidene)-β-L-threo-xylofuranose

Chemical Property:

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Technology Process of 5-(O-p-toluenesulfonyl)-4-C-(p-toluenesulfonyloxymethyl)-1,2-O-(isopropylidene)-β-L-threo-xylofuranose

There total 3 articles about 5-(O-p-toluenesulfonyl)-4-C-(p-toluenesulfonyloxymethyl)-1,2-O-(isopropylidene)-β-L-threo-xylofuranose which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 63.0%

3-O-benzyl-5-(O-p-toluenesulfonyl)-4-C-(p-toluenesulfonyloxymethyl)-1,2-O-(isopropylidene)-β-L-threo-xylofuranose (72261-46-2) → 5-(O-p-toluenesulfonyl)-4-C-(p-toluenesulfonyloxymethyl)-1,2-O-(isopropylidene)-β-L-threo-xylofuranose (551934-26-0)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethyl acetate; at 25 - 28 ℃; for 24h;

DOI:10.1016/S0040-4020(02)01632-0

Reference yield:

1,2-O-isopropylidene-3-O-benzyl-4-C-(hydroxymethyl)-β-L-threo-pento-1,4-furanose (72261-44-0) → 5-(O-p-toluenesulfonyl)-4-C-(p-toluenesulfonyloxymethyl)-1,2-O-(isopropylidene)-β-L-threo-xylofuranose (551934-26-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 76 percent / pyridine / 0 °C

2: 63 percent / hydrogen / Pd/C / ethyl acetate / 24 h / 25 - 28 °C

With pyridine; hydrogen; palladium on activated charcoal; In ethyl acetate;

DOI:10.1016/S0040-4020(02)01632-0

Reference yield:

p-toluenesulfonyl chloride (98-59-9) → 5-(O-p-toluenesulfonyl)-4-C-(p-toluenesulfonyloxymethyl)-1,2-O-(isopropylidene)-β-L-threo-xylofuranose (551934-26-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 76 percent / pyridine / 0 °C

2: 63 percent / hydrogen / Pd/C / ethyl acetate / 24 h / 25 - 28 °C

With pyridine; hydrogen; palladium on activated charcoal; In ethyl acetate;

DOI:10.1016/S0040-4020(02)01632-0

upstream raw materials:

3-O-benzyl-5-(O-p-toluenesulfonyl)-4-C-(p-toluenesulfonyloxymethyl)-1,2-O-(isopropylidene)-β-L-threo-xylofuranose

1,2-O-isopropylidene-3-O-benzyl-4-C-(hydroxymethyl)-β-L-threo-pento-1,4-furanose

p-toluenesulfonyl chloride

Downstream raw materials:

3-O,4-C-methylene-1,2-O-(1-methylethylidene)-5-O-(p-toluenesulfonyl)-β-L-arabinofuranose

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